Certain pyridine derivatives and the use thereof as fungicides

ABSTRACT

Pyridines of the formula ##STR1## where R 1  is hydrogen, C 1  -C 6  -alkyl, C 3  -C 6  -alkenyl, C 3  -C 6  -alkynyl or an acyl radical COR 2  ; R 2  is C 1  -C 6  -alkyl, C 3  -C 6  -alkenyl, C 3  -C 6  -alkynyl, C 1  -C 6  -haloalkyl or substituted or unsubstituted aryl; A is one of the groups ##STR2## where R 3  and R 4  are identical or differ and each is C 1  -C 6  -alkyl, with the proviso that R 3  and R 4  are not simultaneously methyl; R 5  is one of the groups (CH 2 ) n , CH 2  OCH 2 , CH 2  S(O) m  CH 2 , CH 2  CH 2  O or CH 2  CH 2  S(O) m , n denoting 1, 2, 3, 4 or 5, and m being 0, 1 or 2; Ar is aryl which is unsubstituted or bears from one to five substituents selected from the group consisting of C 1  -C 6  -alkyl, phenyl, halogen, C 1  -C 6  -haloalkyl, C 1  -C 6  -alkoxy, C 1  -C 6  -haloalkoxy, C 1  -C 6  -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, and the N-oxides and plant-tolerated acid addition salts thereof, and fungicides containing these compounds.

This is a continuation of application Ser. No. 07/502,401, filed on Mar. 30, 1990, now U.S. Pat. No. 5,112,828.

The present invention relates to novel pyridine derivatives, the N-oxides and salts thereof, to a process for the preparation thereof and the use thereof for controlling fungi.

The novel pyridine derivatives have the formula ##STR3## where R¹ is hydrogen, C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl or COR² ;

R¹ is C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -haloalkyl or substituted or unsubstituted aryl;

A is ##STR4## R³ and R⁴ are, independently of one another, C₁ -C₆ -alkyl with the proviso that R³ and R⁴ are not both methyl;

R⁵ is (CH₂)_(n), CH₂ OCH₂, CH₂ S(O)_(m) CH₂, CH₂ CH₂ O, CH₂ CH₂ S(O)_(m) where

n is an integer from 1 to 5 and

m is an integer from 0 to 2;

Ar is aryl which carries 0-5 substituents from the group comprising C₁ -C₆ -alkyl, phenyl, halogen, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxyiminomethyl, phenoxy, halophenoxy and benzyloxy, and the N-oxides and the acid addition salts which are tolerated by plants of the pyridine compounds.

Examples of R¹ are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso-pentyl, n-hexyl; allyl, 2-methylallyl, 3-methylallyl, 3,3-dimethylallyl; propargyl.

Examples of R² are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentenyl, neo-pentyl, n-hexyl; trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, 2-bromoethyl, 2-chloroethyl, 3-bromopropyl, 4-bromobutyl; aryl which carries zero to three substituents selected from the group comprising C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, halogen, cyano and nitro, such as naphthyl, phenyl, mono-, di- or trimethylphenyl, 4-tert-butylphenyl, mono-, di- or trimethoxyphenyl, trifluoromethylphenyl, fluorophenyl, mono-, di- or trichlorophenyl, mono- or dinitrophenyl and cyanophenyl.

Examples of R³ and R⁴ are, independently of one another, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and n-hexyl.

Examples of R⁵ are methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,5-pentylene, oxydimethylene, ethyleneoxy, thiodimethylene, sulfinyldimethylene, sulfonyldimethylene, ethylenethio, ethylenesulfinyl and ethylenesulfonyl.

Examples of Ar are phenyl, naphthyl, indanyl, mono-, di-, tri- or tetramethylphenyl, ethylphenyl, propylphenyl, isopropylphenyl, butylphenyl, tert-butylphenyl, biphenyl, methylnaphthyl, mono- or difluorophenyl, methylfluorophenyl, tri-, tetra- or pentafluorophenyl, fluorochlorophenyl, methylchlorophenyl, mono-, di-, tri-, tetra- or pentachlorophenyl, bromophenyl, fluorobromophenyl, mono- or bis-trifluoromethylphenyl, mono-, di- or trimethoxyphenyl, ethoxyphenyl, trifluoromethoxyphenyl, tetrafluoroethoxyphenyl, methoxyiminomethylphenyl, ethoxyiminomethylphenyl, phenoxyphenyl, fluorophenoxyphenyl, chlorophenoxyphenyl, chlorophenoxychlorophenyl and benzyloxyphenyl.

Preferred compounds of the formula 1 are those in which

R¹ is hydrogen, methyl, ethyl, tert-butyl, allyl, propargyl or COR²,

R² is C₁ -C₆ -alkyl, C₁ -C₆ -haloalkyl or substituted or unsubstituted phenyl,

A is ##STR5## R³ and R⁴ are, independently of one another, methyl, ethyl, n-propyl, n-butyl, n-pentyl and n-hexyl,

R⁵ is ethylene or 1,3-propylene, and Ar has the meanings specified in claim 1.

The present invention also relates to the N-oxides and the acid addition salts which are tolerated by plants of the novel pyridine derivatives. Examples of salts which are tolerated by plants of the pyridines are salts with mineral acids such as hydrochlorides, hydrobromides, sulfates, nitrates and phosphates; salts with alkanecarboxylic acids such as formates, acetates, propionates, 2-ethylhexanoates and oxalates; salts with arenesulfonic acids such as benzenesulfonates, toluenesulfonates and dodecylbenzenesulfonates.

The compounds of the formula 1 can contain two centers of asymmetry and thus exist in two diastereomeric forms which can be separated by conventional processes, for example by chromatography or crystallization. The present invention embraces both the individual diastereomers and the mixtures thereof and fungicides containing these compounds.

The compounds of the formula 1 have a good fungicidal action which is better than the action of conventional fungicides.

The use of pyridylcarbinols, e.g. 3-phenyl-2,2-dimethyl-1-(3-pyridyl)-1-propanol which is disclosed in EP 302 365, as fungicides has been disclosed. Their fungicidal action is, however, not always entirely satisfactory for certain indications, especially at low application rates.

The process for the preparation of the novel compounds of the formula 1 comprises an aldehyde of the formula 2

    Ar--CH.sub.2 --A--CHO                                      2

in which Ar and A have the meanings specified in claim 1, being reacted with an organometallic compound of the formula 3 ##STR6## in which M is lithium or MgCl, MgBr or MgI, and the resulting pyridyl alcohol of the formula 1 in which A and Ar have the meanings specified in claim 1, and R¹ is hydrogen, being either alkylated with a compound of the formula 4 or acylated with a compound of the formula 5 ##STR7## in which R¹ and R² have the meanings specified in claim 1 with the exception of hydrogen, and X and Y are nucleofugic groups.

Examples of X are chlorine, bromine, iodine, OSO₂ CH₃, OSO₂ C₆ H₅ and OSO₂ --C₆ H₄ --CH₃ (p).

Examples of Y are chlorine, bromine, iodine, ##STR8## or 1-imidazolyl.

The procedure for this reaction is such that, for example, a mixture of pyridyl alcohol of the formula 1 in which R¹ is hydrogen is introduced into at least the equimolar amount of an auxiliary base, with or without an inert organic solvent such as diethyl ether, tetrahydrofuran, dioxane, dimethylformamide, dimethyl sulfoxide, acetonitrile, toluene or xylene, and then the alkylating or acylating agent is metered in.

The reaction is carried out at from 0° to 120° C., preferably 20° to 80° C., for example.

Auxiliary bases which can be used are inorganic and organic acid-binding agents.

Examples of inorganic bases are sodium hydride, sodamide, sodium hydroxide, sodium carbonate, potassium carbonate, potassium hydroxide etc.

Examples of organic bases are amines, especially tertiary amines such as triethylamine, ethyldiisopropylamine and pyridine, and alcoholates such as sodium methylate, sodium ethylate and potassium tert-butylate.

An occasionally advantageous variant of this process entails reacting the pyridyl alcohols of the formula 1 with alkylating agents of the formula 4 in a two-phase system composed of aqueous sodium hydroxide solution and an organic solvent, preferably toluene or dichloromethane, with the addition of a phase-transfer catalyst, e.g. tetra-n-butylammonium chloride, benzyltriethylammonium chloride or methyltrioctylammonium chloride.

The novel pyridyl alcohols of the formula 1 in which R¹ is hydrogen can be prepared, for example, by reacting a metalated pyridine of the formula 3 in which M is lithium or MgCl, MgBr or MgI with an aldehyde of the formula 2 in which Ar and A have the meanings specified in claim 1, e.g. in the presence of a suitable solvent.

This advantageously entails the organometallic compound of the formula 3 being introduced into an inert solvent, preferably an ether such as diethyl ether or tetrahydrofuran, at from -100° to +20° C., preferably from -70° to 0° C., and adding the aldehyde of the formula 2, which may be dissolved in a diluent, dropwise.

The metalated pyridines of the formula 3 are known and can be prepared from the corresponding 3-halopyridines (cf. e.g. N. Furukawa et al., Tetrahedron Letters 1987, 5845 for M=MgBr; A. Fischer and M. W. Morgan, J. Organomet. Chem. 136 (1977) 323 for M=Li).

Some of the aldehydes of the formula 2 are known, and they can be prepared by known processes by alkylating aldehydes of the formula 6 in which A has the meanings specified in claim 1 with a benzyl halide of the formula 7: ##STR9##

It is known that direct α-alkylation of aldehydes usually takes place with only poor yields; the same applies to the enamines derived from the aldehydes (cf. e.g. G. Opitz et al., Liebigs Ann. Chem. 649 (1961) 36). Better results are obtained when the aldehydes of the formula 6 are first converted into N-metalated imines which are then alkylated with benzyl halides (cf. H. Normant et al., Bull. Soc. Chim. Fr. 1970, 3976). A more straightforward method is phase-transfer catalyzed α-alkylation of aldehydes. This process can be carried out as the solid/liquid variant in a two-phase system composed of solid sodium hydroxide and a lipophilic organic solvent (cf. V. G. Poruhit and R. Subramanian, Chem. Ind. (London) 1978, 731) or as the liquid/liquid variant in a two-phase system composed of concentrated sodium hydroxide solution and a lipophilic organic solvent (cf. H. K. Dietl and K. C. Brannock, Tetrahedron Lett. 1973, 1273; E. Buschmann and B. Zeeh, Liebigs Ann. Chem. 1979, 1585).

Another process for the preparation of aldehydes of the formula 2 comprises alkylating nitriles of the formula 8 with benzyl halides of the formula 7, and converting the reaction products of the formula 9 with a suitable reducing agent into the aldehydes 2: ##STR10##

The α-alkylation of nitriles and the reduction of nitriles to aldehydes are known reactions (cf. e.g. D. S. Watt et al., Org. React. 31 (1984) 1 et seq.; M. Rabinovitz in Z. Rappoport (Ed.) "The Chemistry of the Cyano Group", pp. 307 et seq., Interscience, New York 1970; J. Malek and M. Cerny, Synthesis 1972, 217; N. M. Yoon and Y. S. Gyoung, J. Org. Chem. 50 (1985) 2443).

The aldehydes 6, nitriles 8 and benzyl halides 7 used as starting materials are known, and most of them are commercially available.

The examples which follow illustrate the preparation of the novel pyridine derivatives.

EXAMPLE 1 2-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)butyl acetate (compound no. 611)

10.2 g (0.10 mol) of acetic anhydride are added dropwise to a solution of 12.1 g (0.04 mol) of 2-(4-chlorobenzyl)-2-ethyl-1-(3-pyridyl)-1-butanol in 50 ml of pyridine at room temperature, and the mixture is then heated at 80° C. for 8 h. The reaction mixture is concentrated, the residue is taken up in 200 ml of dichloromethane, and the solution is washed with saturated NaHCO₃ solution and then with water. The organic phase is dried and concentrated, and the remaining black oil is purified on silica gel (mobile phase: 5:1 cyclohexane/ethyl acetate). 11.2 g (81% of theory) of the title compound are obtained as a viscous yellow oil. ¹ H-NMR (CDCl₃): δ=8.60(2-Hpy), 8.52(6-Hpy), 7.65(4-Hpy), 7.30(5-Hpy), 7.25(2Hm), 7.05(2Ho), 5.62(CHOAc), 2.68(CH₂ Ar), 2.08(COCH₃), 1.45(CH₂), 1.30(CH₂), 0.95(CH₃), 0.83(CH₃).

EXAMPLE 2 2-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)-1-butanol (compound no. 113)

A solution of 15.8 g of 3-bromopyridine (0.10 mol) in 50 ml of diethyl ether is added dropwise to a mixture of 82 ml of a 1.6M n-butyllithium solution in n-hexane (0.13 mol) under a nitrogen atmosphere at -70° C. The mixture is stirred at -70° C. for 10 minutes and then a solution of 24.7 g of 2-(4-chlorobenzyl)-2-ethylbutanal (0.11 mol) in 50 ml of diethyl ether is added dropwise. After 1 h at -70° C., the mixture is allowed to warm slowly to room temperature and is hydrolyzed with saturated aqueous ammonium chloride solution. The mixture is acidified with dilute hydrochloric acid, and the aqueous phase is separated off and washed with ether and then adjusted to pH 10 to 11 with concentrated ammonia solution while cooling. It is extracted three times with dichloromethane, and the organic phase is dried over Na₂ SO₄ and concentrated. The solid crude product is recrystallized from ethyl acetate/hexane (1:1). 19.2 g (63% of theory) of colorless crystals of melting point 128°-129° C.

Preparation of the starting compound 2-(4-Chlorobenzyl)-2-ethylbutanal

300 ml of toluene, 400 ml of 30 percent (by weight) sodium hydroxide solution and 5.0 g of tetra-n-butyl-ammonium iodide are heated at 80° C. while stirring. To this is slowly added dropwise a mixture of 110 g (1.10 mol) of 2-ethylbutanal and 161 g (1.00 mol) of 4-chlorobenzyl chloride. The mixture is then stirred at 80° C. for 4 h and at room temperature for 14 h, 1,000 ml of toluene are added, and the phases are separated. The organic phase is washed with water, dried over Na₂ SO₄ and concentrated. Fractional distillation results in 123 g (54% of theory) of 2-(4-chlorobenzyl) -2-ethylbutanal as a colorless liquid of boiling point 146°-148° C. at 1 mbar.

The following compounds can also be prepared in a manner corresponding to that in Examples 1 and 2:

                  TABLE 1                                                          ______________________________________                                          ##STR11##                                                                     Ex.                                 Physical                                   no.  A           Ar                 data                                       ______________________________________                                          1   C(CH.sub.3)C.sub.2 H.sub.5                                                                 phenyl                                                         2   C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-methylphenyl                                                 3   C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-methylphenyl                                                 4   C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-methylphenyl                                                 5   C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3-dimethylphenyl                                             6   C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4-dimethylphenyl                                             7   C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,5-dimethylphenyl                                             8   C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,6-dimethylphenyl                                             9   C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,4-dimethylphenyl                                             10  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,5-dimethylphenyl                                             11  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4,5-trimethylphenyl                                          12  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4,6-trimethylphenyl                                          13  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3,5,6-tetramethylphenyl                                      14  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-ethylphenyl                                                  15  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-isopropylphenyl                                              16  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-tert.butylphenyl                                             17  C(CH.sub.3)C.sub.2 H.sub.5                                                                 5-indanyl                                                      18  C(CH.sub. 3)C.sub.2 H.sub.5                                                                1-naphthyl                                                     19  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-naphthyl                                                     20  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-methyl-1-naphthyl                                            21  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-biphenyl                                                     22  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-fluorophenyl                                                 23  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-fluorophenyl                                                 24  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-fluorophenyl                                                 25  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3-difluorophenyl                                             26  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4-difluorophenyl                                             27  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,5-difluorophenyl                                             28  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,6-difluorophenyl                                             29  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,4-difluorophenyl                                             30  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,5-difluorophenyl                                             31  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-fluoro-3-methylphenyl                                        32  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3,5,6-tetrafluorophenyl                                      33  C(CH.sub.3)C.sub.2 H.sub.5                                                                 pentafluorophenyl                                              34  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-chlorophenyl                                                 35  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-chlorophenyl                                                 36  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-chlorophenyl                                                 37  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3-dichlorophenyl                                             38  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4-dichlorophenyl                                             39  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,5-dichlorophenyl                                             40  C(CH.sub.3)C.sub. 2 H.sub.5                                                                2,6-dichlorophenyl                                             41  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,4-dichlorophenyl                                             42  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,5-dichlorophenyl                                             43  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4,5-trichlorophenyl                                          44  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4,6-trichlorophenyl                                          45  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,3,6-trichlorophenyl                                          46  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-chloro-5-methylphenyl                                        47  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-chloro-4-methylphenyl                                        48  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-chloro-4-fluorophenyl                                        49  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-chloro-6-fluorophenyl                                        50  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-chloro-2-fluorophenyl                                        51  C(CH.sub.3)C.sub.2 H.sub.5                                                                 pentachlorophenyl                                              52  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-bromophenyl                                                  53  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-bromophenyl                                                  54  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-bromophenyl                                                  55  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-fluoro-4-bromophenyl                                         56  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-trifluoromethylphenyl                                        57  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-trifluoromethylphenyl                                        58  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-trifluoromethylphenyl                                        59  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2,4-bis(trifluoromethyl)phenyl                                 60  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,5-bis(trifluoromethyl)phenyl                                 61  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-methoxyphenyl                                                62  C(CH.sub.3)C.sub.2 H.sub. 5                                                                3-methoxyphenyl                                                63  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-methoxyphenyl                                                64  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,4-dimethoxyphenyl                                            65  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3,4,5-trimethoxyphenyl                                         66  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-ethoxyphenyl                                                 67  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-tetrafluoroethoxyphenyl                                      68  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-trifluoromethoxyphenyl                                       69  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-methoxyiminocarbyl-phenyl                                    70  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-ethoxyiminocarbyl-phenyl                                     71  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-methoxy-3-methylphenyl                                       72  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-phenoxyphenyl                                                73  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-phenoxyphenyl                                                74  C(CH.sub.3)C.sub.2 H.sub.5                                                                 2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                                 75  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-(4'-chlorophenoxy)-                                                          phenyl)                                                        76  C(CH.sub.3)C.sub.2 H.sub.5                                                                 3-(4'-fluorophenoxy)-                                                          phenyl                                                         77  C(CH.sub.3)C.sub.2 H.sub.5                                                                 4-benzyloxyphenyl                                              78  C(C.sub.2 H.sub.5).sub.2                                                                   phenyl             mp. 130-                                                                       132                                         79  C(C.sub.2 H.sub.5).sub.2                                                                   2-methylphenyl     mp. 92-                                                                        94                                          80  C(C.sub.2 H.sub.5).sub.2                                                                   3-methylphenyl                                                 81  C(C.sub.2 H.sub.5).sub.2                                                                   4-methylphenyl     mp. 87-                                                                        88                                          82  C(C.sub.2 H.sub.5).sub.2                                                                   2,3-dimethylphenyl                                             83  C(C.sub.2 H.sub.5).sub.2                                                                   2,4-dimethylphenyl                                             84  C(C.sub.2 H.sub.5).sub.2                                                                   2,5-dimethylphenyl                                             85  C(C.sub.2 H.sub.5).sub.2                                                                   2,6-dimethylphenyl                                             86  C(C.sub.2 H.sub.5).sub.2                                                                   3,4-dimethylphenyl                                             87  C(C.sub.2 H.sub.5).sub.2                                                                   3,5-dimethylphenyl                                             88  C(C.sub.2 H.sub.5).sub.2                                                                   2,4,5-trimethylphenyl                                          89  C(C.sub.2 H.sub.5).sub.2                                                                   2,4,6-trimethylphenyl                                          90  C(C.sub.2 H.sub.5).sub.2                                                                   2,3,5,6-tetramethylphenyl                                      91  C(C.sub.2 H.sub.5).sub.2                                                                   4-ethylphenyl                                                  92  C(C.sub.2 H.sub.5).sub.2                                                                   4-isopropylphenyl                                              93  C(C.sub.2 H.sub.5).sub.2                                                                   4-tert.butylphenyl mp. 122-                                                                       124                                         94  C(C.sub.2 H.sub.5).sub.2                                                                   5-indanyl                                                      95  C(C.sub.2 H.sub.5).sub.2                                                                   1-naphthyl         mp. 112-                                                                       113                                         96  C(C.sub.2 H.sub.5).sub.2                                                                   2-naphthyl                                                     97  C(C.sub.2 H.sub.5).sub.2                                                                   2-methyl-1-naphthyl                                            98  C(C.sub.2 H.sub.5).sub.2                                                                   4-biphenyl                                                     99  C(C.sub.2 H.sub.5).sub.2                                                                   2-fluorophenyl                                                100  C(C.sub.2 H.sub.5).sub.2                                                                   3-fluorophenyl     mp. 120-                                                                       122                                        101  C(C.sub.2 H.sub.5).sub.2                                                                   4-fluorophenyl     mp. 148-                                                                       150                                        102  C(C.sub.2 H.sub.5).sub.2                                                                   2,3-difluorophenyl                                            103  C(C.sub.2 H.sub.5).sub.2                                                                   2,4-difluorophenyl                                            104  C(C.sub.2 H.sub.5).sub.2                                                                   2,5-difluorophenyl                                            105  C(C.sub.2 H.sub.5).sub.2                                                                   2,6-difluorophenyl                                            106  C(C.sub.2 H.sub.5).sub.2                                                                   3,4-difluorophenyl                                            107  C(C.sub.2 H.sub.5).sub.2                                                                   3,5-difluorophenyl                                            108  C(C.sub.2 H.sub.5).sub.2                                                                   2-fluoro-3-methylphenyl                                       109  C(C.sub.2 H.sub.5).sub.2                                                                   2,3,5,6-tetrafluorophenyl                                     110  C(C.sub.2 H.sub.5).sub.2                                                                   pentafluorophenyl                                             111  C(C.sub.2 H.sub.5).sub.2                                                                   2-chlorophenyl     mp. 96-                                                                        98                                         112  C(C.sub.2 H.sub.5).sub.2                                                                   3-chlorophenyl                                                113  C(C.sub.2 H.sub.5).sub.2                                                                   4-chlorophenyl     mp. 128-                                                                       129                                        114  C(C.sub.2 H.sub.5).sub.2                                                                   2,3-dichlorophenyl                                            115  C(C.sub.2 H.sub.5).sub.2                                                                   2,4-dichlorophenyl mp. 139-                                                                       140                                        116  C(C.sub.2 H.sub.5).sub.2                                                                   2,5-dichlorophenyl                                            117  C(C.sub.2 H.sub.5).sub.2                                                                   2,6-dichlorophenyl                                            118  C(C.sub.2 H.sub.5).sub.2                                                                   3,4-dichlorophenyl                                            119  C(C.sub.2 H.sub.5).sub.2                                                                   3,5-dichlorophenyl                                            120  C(C.sub.2 H.sub.5).sub.2                                                                   2,4,5-trichlorophenyl                                         121  C(C.sub.2 H.sub.5).sub.2                                                                   2,4,6-trichlorophenyl                                         122  C(C.sub.2 H.sub.5).sub.2                                                                   2,3,6-trichlorophenyl                                         123  C(C.sub.2 H.sub.5).sub.2                                                                   2-chloro-5-methylphenyl                                       124  C(C.sub.2 H.sub.5).sub.2                                                                   3-chloro-4-methylphenyl                                       125  C(C.sub.2 H.sub.5).sub.2                                                                   2-chloro-4-fluorophenyl                                       126  C(C.sub.2 H.sub.5).sub.2                                                                   2-chloro-6-fluorophenyl                                       127  C(C.sub.2 H.sub.5).sub.2                                                                   3-chloro-2-fluorophenyl                                       128  C(C.sub.2 H.sub.5).sub.2                                                                   pentachlorophenyl                                             129  C(C.sub.2 H.sub.5).sub.2                                                                   2-bromophenyl                                                 130  C(C.sub.2 H.sub.5).sub.2                                                                   3-bromophenyl                                                 131  C(C.sub.2 H.sub.5).sub.2                                                                   4-bromophenyl                                                 132  C(C.sub.2 H.sub.5).sub.2                                                                   2-fluoro-4-bromophenyl                                        133  C(C.sub.2 H.sub.5).sub.2                                                                   2-trifluoromethylphenyl                                       134  C(C.sub.2 H.sub.5).sub.2                                                                   3-trifluoromethylphenyl                                       135  C(C.sub.2 H.sub.5).sub.2                                                                   4-trifluoromethylphenyl                                       136  C(C.sub.2 H.sub.5).sub.2                                                                   2,4-bis(trifluoromethyl)phenyl                                137  C(C.sub.2 H.sub.5).sub.2                                                                   3,5-bis(trifluoromethyl)phenyl                                138  C(C.sub.2 H.sub.5).sub.2                                                                   2-methoxyphenyl                                               139  C(C.sub.2 H.sub.5).sub.2                                                                   3-methoxyphenyl                                               140  C(C.sub.2 H.sub.5).sub.2                                                                   4-methoxyphenyl                                               141  C(C.sub.2 H.sub.5).sub.2                                                                   3,4-dimethoxyphenyl                                           142  C(C.sub.2 H.sub.5).sub.2                                                                   3,4,5-trimethoxyphenyl                                        143  C(C.sub.2 H.sub.5).sub.2                                                                   4-ethoxyphenyl                                                144  C(C.sub.2 H.sub.5).sub.2                                                                   4-tetrafluoroethoxyphenyl                                     145  C(C.sub.2 H.sub.5).sub.2                                                                   4-trifluoromethoxyphenyl                                      146  C(C.sub.2 H.sub.5).sub.2                                                                   4-methoxyiminocarbyl-phenyl                                   147  C(C.sub.2 H.sub.5).sub.2                                                                   4-ethoxyiminocarbyl-phenyl                                    148  C(C.sub.2 H.sub.5).sub.2                                                                   4-methoxy-3-methylphenyl                                      149  C(C.sub.2 H.sub.5).sub.2                                                                   3-phenoxyphenyl                                               150  C(C.sub.2 H.sub.5).sub.2                                                                   4-phenoxyphenyl                                               151  C(C.sub.2 H.sub.5).sub.2                                                                   2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                                152  C(C.sub.2 H.sub.5).sub.2                                                                   4-(4'-chlorophenoxy)-                                                          phenyl)                                                       153  C(C.sub.2 H.sub.5).sub.2                                                                   4-benzyloxyphenyl                                             154  C(CH.sub.2).sub.4                                                                          phenyl                                                        155  C(CH.sub.2).sub.4                                                                          2-methylphenyl                                                156  C(CH.sub.2).sub.4                                                                          3-methylphenyl                                                157  C(CH.sub.2).sub.4                                                                          4-methylphenyl                                                158  C(CH.sub.2).sub.4                                                                          2,3-dimethylphenyl                                            159  C(CH.sub.2).sub.4                                                                          2,4-dimethylphenyl                                            160  C(CH.sub.2).sub.4                                                                          2,5-dimethylphenyl                                            161  C(CH.sub.2).sub.4                                                                          2,6-dimethylphenyl                                            162  C(CH.sub.2).sub.4                                                                          3,4-dimethylphenyl                                            163  C(CH.sub.2).sub.4                                                                          3,5-dimethylphenyl                                            164  C(CH.sub.2).sub.4                                                                          2,4,5-trimethylphenyl                                         165  C(CH.sub.2).sub.4                                                                          2,4,6-trimethylphenyl                                         166  C(CH.sub.2).sub.4                                                                          2,3,5,6-tetramethylphenyl                                     167  C(CH.sub.2).sub.4                                                                          4-ethylphenyl                                                 168  C(CH.sub.2).sub.4                                                                          4-isopropylphenyl                                             169  C(CH.sub.2).sub.4                                                                          4-tert.butylphenyl                                            170  C(CH.sub.2).sub.4                                                                          5-indanyl                                                     171  C(CH.sub.2).sub.4                                                                          1-naphthyl                                                    172  C(CH.sub.2).sub.4                                                                          2-naphthyl                                                    173  C(CH.sub.2).sub.4                                                                          2-methyl-1-napthyl                                            174  C(CH.sub.2).sub.4                                                                          4-biphenyl                                                    175  C(CH.sub.2).sub.4                                                                          2-fluorophenyl     mp. 75-                                                                        76                                         176  C(CH.sub.2).sub.4                                                                          3-fluorophenyl                                                177  C(CH.sub.2).sub.4                                                                          4-fluorophenyl     mp. 166-                                                                       168                                        178  C(CH.sub.2).sub.4                                                                          2,3-difluorophenyl                                            179  C(CH.sub.2).sub.4                                                                          2,4-difluorophenyl                                            180  C(CH.sub.2).sub.4                                                                          2,5-difluorophenyl                                            181  C(CH.sub.2).sub.4                                                                          2,6-difluorophenyl                                            182  C(CH.sub.2).sub.4                                                                          3,4-difluorophenyl                                            183  C(CH.sub.2).sub.4                                                                          3,5-difluorophenyl                                            184  C(CH.sub.2).sub.4                                                                          2-fluoro-3-methylphenyl                                       185  C(CH.sub.2).sub.4                                                                          2,3,5,6-tetrafluorophenyl                                     186  C(CH.sub.2).sub.4                                                                          pentafluorophenyl                                             187  C(CH.sub.2).sub.4                                                                          2-chlorophenyl     mp. 114-                                                                       116                                        188  C(CH.sub.2).sub.4                                                                          3-chlorophenyl                                                189  C(CH.sub.2).sub.4                                                                          4-chlorophenyl     mp. 162-                                                                       164                                        190  C(CH.sub.2).sub.4                                                                          2,3-dichlorophenyl                                            191  C(CH.sub.2).sub.4                                                                          2,4-dichlorophenyl mp. 110-                                                                       112                                        192  C(CH.sub.2).sub.4                                                                          2,5-dichlorophenyl                                            193  C(CH.sub.2).sub.4                                                                          2,6-dichlorophenyl                                            194  C(CH.sub.2).sub.4                                                                          3,4-dichlorophenyl                                            195  C(CH.sub.2).sub.4                                                                          3,5-dichlorophenyl                                            196  C(CH.sub.2).sub.4                                                                          2,4,5-trichlorophenyl                                         197  C(CH.sub.2).sub.4                                                                          2,4,6-trichlorophenyl                                         198  C(CH.sub.2).sub.4                                                                          2,3,6-trichlorophenyl                                         199  C(CH.sub.2).sub.4                                                                          2-chloro-5-methylphenyl                                       200  C(CH.sub.2).sub.4                                                                          3-chloro-4-methylphenyl                                       201  C(CH.sub.2).sub.4                                                                          2-chloro-4-fluorophenyl                                       202  C(CH.sub.2).sub.4                                                                          2-chloro-6-fluorophenyl                                       203  C(CH.sub.2).sub.4                                                                          3-chloro-2-fluorophenyl                                       204  C(CH.sub.2).sub.4                                                                          pentachlorophenyl                                             205  C(CH.sub.2).sub.4                                                                          2-bromophenyl                                                 206  C(CH.sub.2).sub.4                                                                          3-bromophenyl                                                 207  C(CH.sub.2).sub.4                                                                          4-bromophenyl                                                 208  C(CH.sub.2).sub.4                                                                          2-fluoro-4-bromophenyl                                        209  C(CH.sub.2).sub.4                                                                          2-trifluoromethylphenyl                                       210  C(CH.sub.2).sub.4                                                                          3-trifluoromethylphenyl                                       211  C(CH.sub.2).sub.4                                                                          4-trifluoromethylphenyl                                       212  C(CH.sub.2).sub.4                                                                          2,4-bis(trifluoromethyl)phenyl                                213  C(CH.sub.2).sub.4                                                                          3,5-bis(trifluoromethyl)phenyl                                214  C(CH.sub.2).sub.4                                                                          2-methoxyphenyl                                               215  C(CH.sub.2).sub.4                                                                          3-methoxyphenyl                                               216  C(CH.sub.2).sub.4                                                                          4-methoxyphenyl                                               217  C(CH.sub.2).sub.4                                                                          3,4-dimethoxyphenyl                                           218  C(CH.sub.2).sub.4                                                                          3,4,5-trimethoxyphenyl                                        219  C(CH.sub.2).sub.4                                                                          4-ethoxyphenyl                                                220  C(CH.sub.2).sub.4                                                                          4-tetrafluoroethoxyphenyl                                     221  C(CH.sub.2).sub.4                                                                          4-trifluoromethoxyphenyl                                      222  C(CH.sub.2).sub.4                                                                          4-methoxyiminocarbyl-phenyl                                   223  C(CH.sub.2).sub.4                                                                          4-ethoxyiminocarbyl-phenyl                                    224  C(CH.sub.2).sub.4                                                                          4-methoxy-3-methylphenyl                                      225  C(CH.sub.2).sub.4                                                                          3-phenoxyphenyl                                               226  C(CH.sub.2).sub.4                                                                          4-phenoxyphenyl                                               227  C(CH.sub.2).sub.4                                                                          2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                                228  C(CH.sub.2).sub.4                                                                          3-(4'-fluorophenoxy)-                                                          phenyl                                                        229  C(CH.sub.2).sub.4                                                                          4-benzyloxyphenyl                                             230  C(CH.sub.2).sub.5                                                                          phenyl             mp. 117-                                                                       119                                        231  C(CH.sub.2).sub.5                                                                          2-methylphenyl                                                232  C(CH.sub.2).sub.5                                                                          3-methylphenyl                                                233  C(CH.sub.2).sub.5                                                                          4-methylphenyl                                                234  C(CH.sub.2).sub.5                                                                          2,3-dimethylphenyl                                            235  C(CH.sub.2).sub.5                                                                          2,4-dimethylphenyl                                            236  C(CH.sub.2).sub.5                                                                          2,5-dimethylphenyl                                            237  C(CH.sub.2).sub.5                                                                          2,6-dimethylphenyl                                            238  C(CH.sub.2).sub.5                                                                          3,4-dimethylphenyl                                            239  C(CH.sub.2).sub.5                                                                          3,5-dimethylphenyl                                            240  C(CH.sub.2).sub.5                                                                          2,4,5-trimethylphenyl                                         241  C(CH.sub.2).sub.5                                                                          2,4,6-trimethylphenyl                                         242  C(CH.sub.2).sub.5                                                                          2,3,5,6-tetramethylphenyl                                     243  C(CH.sub.2).sub.5                                                                          4-ethylphenyl                                                 244  C(CH.sub.2).sub.5                                                                          4-isopropylphenyl                                             245  C(CH.sub.2).sub.5                                                                          4-tert.butylphenyl                                            246  C(CH.sub.2).sub.5                                                                          5-indanyl                                                     247  C(CH.sub.2).sub.5                                                                          1-naphthyl                                                    248  C(CH.sub.2).sub.5                                                                          2-naphthyl                                                    249  C(CH.sub.2).sub.5                                                                          2-methyl-1-napthyl                                            250  C(CH.sub.2).sub.5                                                                          4-biphenyl                                                    251  C(CH.sub.2).sub.5                                                                          2-fluorophenyl     mp. 146-                                                                       148                                        252  C(CH.sub.2).sub.5                                                                          3-fluorophenyl     mp. 132-                                                                       134                                        253  C(CH.sub.2).sub.5                                                                          4-fluorophenyl     mp. 126-                                                                       127                                        254  C(CH.sub.2).sub.5                                                                          2,3-difluorophenyl                                            255  C(CH.sub.2).sub.5                                                                          2,4-difluorophenyl                                            256  C(CH.sub.2).sub.5                                                                          2,5-difluorophenyl                                            257  C(CH.sub.2).sub.5                                                                          2,6-difluorophenyl                                            258  C(CH.sub.2).sub.5                                                                          3,4-difluorophenyl                                            259  C(CH.sub.2).sub.5                                                                          3,5-difluorophenyl                                            260  C(CH.sub.2).sub.5                                                                          2-fluoro-3-methylphenyl                                       261  C(CH.sub.2).sub.5                                                                          2,3,5,6-tetrafluorophenyl                                     262  C(CH.sub.2).sub.5                                                                          pentafluorophenyl                                             263  C(CH.sub.2).sub.5                                                                          2-chlorophenyl     mp. 162-                                                                       164                                        264  C(CH.sub.2).sub.5                                                                          3-chlorophenyl                                                265  C(CH.sub.2).sub.5                                                                          4-chlorophenyl     mp. 155-                                                                       156                                        266  C(CH.sub.2).sub.5                                                                          2,3-dichlorophenyl                                            267  C(CH.sub.2).sub.5                                                                          2,4-dichlorophenyl oil;                                                                           N-oxide                                                                        mp. 205-                                                                       207                                        268  C(CH.sub.2).sub.5                                                                          2,5-dichlorophenyl                                            269  C(CH.sub.2).sub.5                                                                          2,6-dichlorophenyl                                            270  C(CH.sub.2).sub.5                                                                          3,4-dichlorophenyl mp. 181-                                                                       183                                        271  C(CH.sub.2).sub.5                                                                          3,5-dichlorophenyl                                            272  C(CH.sub.2).sub.5                                                                          2,4,5-trichlorophenyl                                         273  C(CH.sub.2).sub.5                                                                          2,4,6-trichlorophenyl                                         274  C(CH.sub.2).sub.5                                                                          2,3,6-trichlorophenyl                                         275  C(CH.sub.2).sub.5                                                                          2-chloro-5-methylphenyl                                       276  C(CH.sub.2).sub.5                                                                          3-chloro-4-methylphenyl                                       277  C(CH.sub.2).sub.5                                                                          2-chloro-4-fluorophenyl                                       278  C(CH.sub.2).sub.5                                                                          2-chloro-6-fluorophenyl                                       279  C(CH.sub.2).sub.5                                                                          3-chloro-2-fluorophenyl                                       280  C(CH.sub.2).sub.5                                                                          pentachlorophenyl                                             281  C(CH.sub.2).sub.5                                                                          2-bromophenyl                                                 282  C(CH.sub.2).sub.5                                                                          3-bromophenyl                                                 283  C(CH.sub.2).sub.5                                                                          4-bromophenyl      mp. 190-                                                                       191                                        284  C(CH.sub.2).sub.5                                                                          2-fluoro-4-bromophenyl                                        285  C(CH.sub.2).sub.5                                                                          2-trifluoromethylphenyl                                       286  C(CH.sub.2).sub.5                                                                          3-trifluoromethylphenyl                                       287  C(CH.sub.2).sub.5                                                                          4-trifluoromethylphenyl                                       288  C(CH.sub.2).sub.5                                                                          2,4-bis(trifluoromethyl)phenyl                                289  C(CH.sub.2).sub.5                                                                          3,5-bis(trifluoromethyl)phenyl                                290  C(CH.sub.2).sub.5                                                                          2-methoxyphenyl                                               291  C(CH.sub.2).sub.5                                                                          3-methoxyphenyl                                               292  C(CH.sub.2).sub.5                                                                          4-methoxyphenyl                                               293  C(CH.sub.2).sub.5                                                                          3,4-dimethoxyphenyl                                           294  C(CH.sub.2).sub.5                                                                          3,4,5-trimethoxyphenyl                                        295  C(CH.sub.2).sub.5                                                                          4-ethoxyphenyl                                                296  C(CH.sub.2).sub.5                                                                          4-tetrafluoroethoxyphenyl                                     297  C(CH.sub.2).sub.5                                                                          4-trifluoromethoxyphenyl                                      298  C(CH.sub.2).sub.5                                                                          4-methoxyiminocarbyl-phenyl                                   299  C(CH.sub.2).sub.5                                                                          4-ethoxyiminocarbyl-phenyl                                    300  C(CH.sub.2).sub.5                                                                          4-methoxy-3-methylphenyl                                      301  C(CH.sub.2).sub.5                                                                          3-phenoxyphenyl                                               302  C(CH.sub.2).sub.5                                                                          4-phenoxyphenyl                                               303  C(CH.sub.2).sub.5                                                                          2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                                304  C(CH.sub.2).sub.5                                                                          3-(4'-fluorophenoxy)-                                                          phenyl                                                        305  C(CH.sub.2).sub.5                                                                          4-benzyloxyphenyl                                             306  C(CH.sub.3)nC.sub.3 H.sub.7                                                                phenyl             oil;                                                                           N-oxide                                                                        mp. 154-                                                                       156                                        307  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-methylphenyl                                                308  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-methylphenyl                                                309  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-methylphenyl                                                310  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3-dimethylphenyl                                            311  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4-dimethylphenyl                                            312  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,5-dimethylphenyl                                            313  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,6-dimethylphenyl                                            314  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,4-dimethylphenyl                                            315  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,5-dimethylphenyl                                            316  C(CH.sub.3)nC.sub.3 H.sub. 7                                                               2,4,5-trimethylphenyl                                         317  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4,6-trimethylphenyl                                         318  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3,5,6-tetramethylphenyl                                     319  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-ethylphenyl                                                 320  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-isopropylphenyl                                             321  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-tert.butylphenyl                                            322  C(CH.sub.3)nC.sub.3 H.sub.7                                                                5-indanyl                                                     323  C(CH.sub.3)nC.sub.3 H.sub.7                                                                1-naphthyl                                                    324  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-naphthyl                                                    325  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-methyl-1-naphthyl                                           326  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-biphenyl                                                    327  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-fluorophenyl                                                328  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-fluorophenyl                                                329  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-fluorophenyl                                                330  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3-difluorophenyl                                            331  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4-difluorophenyl                                            332  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,5-difluorophenyl                                            333  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,6-difluorophenyl                                            334  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,4-difluorophenyl                                            335  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,5-difluorophenyl                                            336  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-fluoro-3-methylphenyl                                       337  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3,5,6-tetrafluorophenyl                                     338  C(CH.sub.3)nC.sub.3 H.sub.7                                                                pentafluorophenyl                                             339  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-chlorophenyl                                                340  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-chlorophenyl                                                341  C(CH.sub.3)nC.sub.3 H.sub. 7                                                               4-chlorophenyl     oil;                                                                           N-oxide:                                                                       mp. 159-                                                                       160                                        342  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3-dichlorophenyl                                            343  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4-dichlorophenyl                                            344  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,5-dichlorophenyl                                            345  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,6-dichlorophenyl                                            346  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,4-dichlorophenyl                                            347  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,5-dichlorophenyl                                            348  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4,5-trichlorophenyl                                         349  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4,6-trichlorophenyl                                         350  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,3,6-trichlorophenyl                                         351  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-chloro-5-methylphenyl                                       352  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-chloro-4-methylphenyl                                       353  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-chloro-4-fluorophenyl                                       354  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-chloro-6-fluorophenyl                                       355  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-chloro-2-fluorophenyl                                       356  C(CH.sub.3)nC.sub.3 H.sub.7                                                                pentachlorophenyl                                             357  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-bromophenyl                                                 358  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-bromophenyl                                                 359  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-bromophenyl                                                 360  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-fluoro-4-bromophenyl                                        361  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-trifluoromethylphenyl                                       362  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-trifluoromethylphenyl                                       363  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-trifluoromethylphenyl                                       364  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2,4-bis(trifluoromethyl)phenyl                                365  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,5-bis(trifluoromethyl)phenyl                                366  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-methoxyphenyl                                               367  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-methoxyphenyl                                               368  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-methoxyphenyl                                               369  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,4-dimethoxyphenyl                                           370  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3,4,5-trimethoxyphenyl                                        371  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-ethoxyphenyl                                                372  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-tetrafluoroethoxyphenyl                                     373  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-trifluoromethoxyphenyl                                      374  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-methoxyiminocarbyl-phenyl                                   375  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-ethoxyiminocarbyl-phenyl                                    376  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-methoxy-3-methylphenyl                                      377  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-phenoxyphenyl                                               378  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-phenoxyphenyl                                               379  C(CH.sub.3)nC.sub.3 H.sub.7                                                                2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                                380  C(CH.sub.3)nC.sub.3 H.sub.7                                                                3-(4'-fluorophenoxy)-                                                          phenyl                                                        381  C(CH.sub.3)nC.sub.3 H.sub.7                                                                4-benzyloxyphenyl                                             382  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         phenyl             oil                                        383  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-methylphenyl                                                384  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-methylphenyl                                                385  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-methylphenyl                                                386  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3-dimethylphenyl                                            387  C(C.sub.2 H.sub. 5)nC.sub.4 H.sub.9                                                        2,4-dimethylphenyl                                            388  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,5-dimethylphenyl                                            389  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,6-dimethylphenyl                                            390  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,4-dimethylphenyl                                            391  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,5-dimethylphenyl                                            392  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4,5-trimethylphenyl                                         393  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4,6-trimethylphenyl                                         394  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3,5,6-tetramethylphenyl                                     395  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-ethylphenyl                                                 396  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-isopropylphenyl                                             397  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-tert.butylphenyl                                            398  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         5-indanyl                                                     399  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         1-naphthyl                                                    400  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-naphthyl                                                    401  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-methyl-1-napthyl                                            402  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-biphenyl                                                    403  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-fluorophenyl                                                404  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-fluorophenyl                                                405  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-fluorophenyl                                                406  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3-difluorophenyl                                            407  C(C.sub.2 H.sub. 5)nC.sub.4 H.sub.9                                                        2,4-difluorophenyl                                            408  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,5-difluorophenyl                                            409  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,6-difluorophenyl                                            410  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,4-difluorophenyl                                            411  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,5-difluorophenyl                                            412  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-fluoro-3-methylphenyl                                       413  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3,5,6-tetrafluorophenyl                                     414  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         pentafluorophenyl                                             415  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-chlorophenyl                                                416  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-chlorophenyl                                                417  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-chlorophenyl                                                418  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3-dichlorophenyl                                            419  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4-dichlorophenyl                                            420  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,5-dichlorophenyl                                            421  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,6-dichlorophenyl                                            422  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,4-dichlorophenyl                                            423  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,5-dichlorophenyl                                            424  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4,5-trichlorophenyl                                         425  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4,6-trichlorophenyl                                         426  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,3,6-trichlorophenyl                                         427  C(C.sub.2 H.sub. 5)nC.sub.4 H.sub.9                                                        2-chloro-5-methylphenyl                                       428  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-chloro-4-methylphenyl                                       429  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-chloro-4-fluorophenyl                                       430  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-chloro-6-fluorophenyl                                       431  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-chloro-2-fluorophenyl                                       432  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         pentachlorophenyl                                             433  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-bromophenyl                                                 434  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-bromophenyl                                                 435  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-bromophenyl                                                 436  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-fluoro-4-bromophenyl                                        437  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-trifluoromethylphenyl                                       438  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-trifluoromethylphenyl                                       439  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-trifluoromethylphenyl                                       440  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2,4-bis(trifluoromethyl)phenyl                                441  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,5-bis(trifluoromethyl)phenyl                                442  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-methoxyphenyl                                               443  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-methoxyphenyl                                               444  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-methoxyphenyl                                               445  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,4-dimethoxyphenyl                                           446  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3,4,5-trimethoxyphenyl                                        447  C(C.sub.2 H.sub. 5)nC.sub.4 H.sub.9                                                        4-ethoxyphenyl                                                448  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-tetrafluoroethoxyphenyl                                     449  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-trifluoromethoxyphenyl                                      450  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-methoxyiminocarbyl-phenyl                                   451  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-ethoxyiminocarbyl-phenyl                                    452  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-methoxy-3-methylphenyl                                      453  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-phenoxyphenyl                                               454  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-phenoxyphenyl                                               455  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                                456  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         3-(4'-fluorophenoxy)-                                                          phenyl                                                        457  C(C.sub.2 H.sub.5)nC.sub.4 H.sub.9                                                         4-benzyloxyphenyl                                             458  C(CH.sub.2).sub.3 OCH.sub.2                                                                phenyl                                                        459  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-methylphenyl                                                460  C(CH.sub.2).sub.3 OCH.sub.2                                                                3-methylphenyl                                                461  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-methylphenyl                                                462  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3-dimethylphenyl                                            463  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4-dimethylphenyl                                            464  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,5-dimethylphenyl                                            465  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,6-dimethylphenyl                                            466  C(CH.sub.2).sub.3 OCH.sub.2                                                                3,4-dimethylphenyl                                            467  C(CH.sub.2).sub.3 OCH.sub.2                                                                3,5-dimethylphenyl                                            468  C(CH.sub.2).sub.3 OCH.sub. 2                                                               2,4,5-trimethylphenyl                                         469  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4,6-trimethylphenyl                                         470  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3,5,6-tetramethylphenyl                                     471  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-ethylphenyl                                                 472  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-isopropylphenyl                                             473  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-tert.butylphenyl                                            474  C(CH.sub.2).sub.3 OCH.sub.2                                                                5-indanyl                                                     475  C(CH.sub.2).sub.3 OCH.sub.2                                                                1-naphthyl                                                    476  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-naphthyl                                                    477  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-methyl-1-naphthyl                                           478  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-biphenyl                                                    479  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-fluorophenyl                                                480  C(CH.sub.2).sub.3 OCH.sub.2                                                                3-fluorophenyl                                                481  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-fluorophenyl                                                482  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3-difluorophenyl                                            483  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4-difluorophenyl                                            484  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,5-difluorophenyl                                            485  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,6-difluorophenyl                                            486  C(CH.sub.2).sub.3 OCH.sub.2                                                                3,4-difluorophenyl                                            487  C(CH.sub.2).sub.3 OCH.sub.2                                                                3,5-difluorophenyl                                            488  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-fluoro-3-methylphenyl                                       489  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3,5,6-tetrafluorophenyl                                     490  C(CH.sub.2).sub.3 OCH.sub.2                                                                pentafluorophenyl                                             491  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-chlorophenyl                                                492  C(CH.sub.2).sub.3 OCH.sub.2                                                                3-chlorophenyl                                                493  C(CH.sub.2).sub.3 OCH.sub. 2                                                               4-chlorophenyl                                                494  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3-dichlorophenyl                                            495  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4-dichlorophenyl                                            496  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,5-dichlorophenyl                                            497  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,6-dichlorophenyl                                            498  C(CH.sub.2).sub.3 OCH.sub.2                                                                3,4-dichlorophenyl                                            499  C(CH.sub.2).sub.3 OCH.sub.2                                                                3,5-dichlorophenyl                                            500  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4,5-trichlorophenyl                                         501  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4,6-trichlorophenyl                                         502  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,3,6-trichlorophenyl                                         503  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-chloro-5-methylphenyl                                       504  C(CH.sub.2).sub.3 OCH.sub.2                                                                3-chloro-4-methylphenyl                                       505  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-chloro-4-fluorophenyl                                       506  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-chloro-6-fluorophenyl                                       507  C(CH.sub.2).sub.3 OCH.sub.2                                                                3-chloro-2-fluorophenyl                                       508  C(CH.sub.2).sub.3 OCH.sub.2                                                                pentachlorophenyl                                             509  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-bromophenyl                                                 510  C(CH.sub.2).sub.3 OCH.sub.2                                                                3-bromophenyl                                                 511  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-bromophenyl                                                 512  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-fluoro-4-bromophenyl                                        513  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-trifluoromethylphenyl                                       514  C(CH.sub.2).sub.3 OCH.sub.2                                                                3-trifluoromethylphenyl                                       515  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-trifluoromethylphenyl                                       516  C(CH.sub.2).sub.3 OCH.sub.2                                                                2,4-bis(trifluoromethyl)phenyl                                517  C(CH.sub.2).sub.3 OCH.sub.2                                                                3,5-bis(trifluoromethyl)phenyl                                518  C(CH.sub.2).sub.3 OCH.sub. 2                                                               2-methoxyphenyl                                               519  C(CH.sub.2).sub.3 OCH.sub.2                                                                3-methoxyphenyl                                               520  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-methoxyphenyl                                               521  C(CH.sub.2).sub.3 OCH.sub.2                                                                3,4-dimethoxyphenyl                                           522  C(CH.sub.2).sub.3 OCH.sub.2                                                                3,4,5-trimethoxyphenyl                                        523  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-ethoxyphenyl                                                524  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-tetrafluoroethoxyphenyl                                     525  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-trifluoromethoxyphenyl                                      526  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-methoxyiminocarbyl-phenyl                                   527  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-ethoxyiminocarbyl-phenyl                                    528  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-methoxy-3-methylphenyl                                      529  C(CH.sub.2).sub.3 OCH.sub.2                                                                3-phenoxyphenyl                                               530  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-phenoxyphenyl                                               531  C(CH.sub.2).sub.3 OCH.sub.2                                                                2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                                532  C(CH.sub.2).sub.3 OCH.sub.2                                                                3-(4'-fluorophenoxy)-                                                          phenyl                                                        533  C(CH.sub.2).sub.3 OCH.sub.2                                                                4-benzyloxyphenyl                                             534  C(CH.sub.2).sub.2                                                                          phenyl                                                        535  C(CH.sub.2).sub.2                                                                          2-methylphenyl                                                536  C(CH.sub.2).sub.2                                                                          3-methylphenyl                                                537  C(CH.sub.2).sub.2                                                                          4-methylphenyl                                                538  C(CH.sub.2).sub.2                                                                          2,3-dimethylphenyl                                            539  C(CH.sub.2).sub.2                                                                          2,4-dimethylphenyl                                            540  C(CH.sub.2).sub.2                                                                          2,5-dimethylphenyl                                            541  C(CH.sub.2).sub.2                                                                          2,6-dimethylphenyl                                            542  C(CH.sub.2).sub.2                                                                          3,4-dimethylphenyl                                            543  C(CH.sub.2).sub.2                                                                          3,5-dimethylphenyl                                            544  C(CH.sub.2).sub.2                                                                          2,4,5-trimethylphenyl                                         545  C(CH.sub.2).sub. 2                                                                         2,4,6-trimethylphenyl                                         546  C(CH.sub.2).sub.2                                                                          2,3,5,6-tetramethylphenyl                                     547  C(CH.sub.2).sub.2                                                                          4-ethylphenyl                                                 548  C(CH.sub.2).sub.2                                                                          4-isopropylphenyl                                             549  C(CH.sub.2).sub.2                                                                          4-tert.butylphenyl                                            550  C(CH.sub.2).sub.2                                                                          5-indanyl                                                     551  C(CH.sub.2).sub.2                                                                          1-naphthyl                                                    552  C(CH.sub.2).sub.2                                                                          2-naphthyl                                                    553  C(CH.sub.2).sub.2                                                                          2-methyl-1-napthyl                                            554  C(CH.sub.2).sub.2                                                                          4-biphenyl                                                    555  C(CH.sub.2).sub.2                                                                          2-fluorophenyl                                                556  C(CH.sub.2).sub.2                                                                          3-fluorophenyl                                                557  C(CH.sub.2).sub.2                                                                          4-fluorophenyl                                                558  C(CH.sub.2).sub.2                                                                          2,3-difluorophenyl                                            559  C(CH.sub.2).sub.2                                                                          2,4-difluorophenyl                                            560  C(CH.sub.2).sub.2                                                                          2,5-difluorophenyl                                            561  C(CH.sub.2).sub.2                                                                          2,6-difluorophenyl                                            562  C(CH.sub.2).sub.2                                                                          3,4-difluorophenyl                                            563  C(CH.sub.2).sub.2                                                                          3,5-difluorophenyl                                            564  C(CH.sub.2).sub.2                                                                          2-fluoro-3-methylphenyl                                       565  C(CH.sub.2).sub.2                                                                          2,3,5,6-tetrafluorophenyl                                     566  C(CH.sub.2).sub.2                                                                          pentafluorophenyl                                             567  C(CH.sub.2).sub.2                                                                          2-chlorophenyl                                                568  C(CH.sub.2).sub.2                                                                          3-chlorophenyl                                                569  C(CH.sub.2).sub.2                                                                          4-chlorophenyl                                                570  C(CH.sub.2).sub.2                                                                          2,3-dichlorophenyl                                            571  C(CH.sub.2).sub.2                                                                          2,4-dichlorophenyl                                            572  C(CH.sub.2).sub.2                                                                          2,5-dichlorophenyl                                            573  C(CH.sub.2).sub.2                                                                          2,6-dichlorophenyl                                            574  C(CH.sub.2).sub.2                                                                          3,4-dichlorophenyl                                            575  C(CH.sub.2).sub.2                                                                          3,5-dichlorophenyl                                            576  C(CH.sub.2).sub.2                                                                          2,4,5-trichlorophenyl                                         577  C(CH.sub.2).sub.2                                                                          2,4,6-trichlorophenyl                                         578  C(CH.sub.2).sub.2                                                                          2,3,6-trichlorophenyl                                         579  C(CH.sub.2).sub.2                                                                          2-chloro-5-methylphenyl                                       580  C(CH.sub.2).sub.2                                                                          3-chloro-4-methylphenyl                                       581  C(CH.sub.2).sub.2                                                                          2-chloro-4-fluorophenyl                                       582  C(CH.sub.2).sub.2                                                                          2-chloro-6-fluorophenyl                                       583  C(CH.sub.2).sub.2                                                                          3-chloro-2-fluorophenyl                                       584  C(CH.sub.2).sub.2                                                                          pentachlorophenyl                                             585  C(CH.sub.2).sub.2                                                                          2-bromophenyl                                                 586  C(CH.sub.2).sub.2                                                                          3-bromophenyl                                                 587  C(CH.sub.2).sub.2                                                                          4-bromophenyl                                                 588  C(CH.sub.2).sub.2                                                                          2-fluoro-4-bromophenyl                                        589  C(CH.sub.2).sub.2                                                                          2-trifluoromethylphenyl                                       590  C(CH.sub.2).sub.2                                                                          3-trifluoromethylphenyl                                       591  C(CH.sub.2).sub.2                                                                          4-trifluoromethylphenyl                                       592  C(CH.sub.2).sub.2                                                                          2,4-bis(trifluoromethyl)phenyl                                593  C(CH.sub.2).sub.2                                                                          3,5-bis(trifluoromethyl)phenyl                                594  C(CH.sub.2).sub.2                                                                          2-methoxyphenyl                                               595  C(CH.sub.2).sub.2                                                                          3-methoxyphenyl                                               596  C(CH.sub.2).sub.2                                                                          4-methoxyphenyl                                               597  C(CH.sub.2).sub.2                                                                          3,4-dimethoxyphenyl                                           598  C(CH.sub.2).sub.2                                                                          3,4,5-trimethoxyphenyl                                        599  C(CH.sub.2).sub.2                                                                          4-ethoxyphenyl                                                600  C(CH.sub.2).sub.2                                                                          4-tetrafluoroethoxyphenyl                                     601  C(CH.sub.2).sub.2                                                                          4-trifluoromethoxyphenyl                                      602  C(CH.sub.2).sub.2                                                                          4-methoxyiminocarbyl-phenyl                                   603  C(CH.sub.2).sub.2                                                                          4-ethoxyiminocarbyl-phenyl                                    604  C(CH.sub.2).sub.2                                                                          4-methoxy-3-methylphenyl                                      605  C(CH.sub.2).sub.2                                                                          3-phenoxyphenyl                                               606  C(CH.sub.2).sub.2                                                                          4-phenoxyphenyl                                               607  C(CH.sub.2).sub.2                                                                          2-chloro-4-(4'-chloro-                                                         phenoxy)phenyl                                                608  C(CH.sub.2).sub.2                                                                          3-(4'-fluorophenoxy)-                                                          phenyl                                                        609  C(CH.sub.2).sub.2                                                                          4-benzyloxyphenyl                                             ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR12##                                                                     Ex.                                                                            no.  R.sup.2                                                                               A           Ar          Physical data                              ______________________________________                                         610  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   phenyl      oil                                        611  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   4-chlorophenyl                                                                             oil                                        612  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   4-fluorophenyl                                                                             oil                                        613  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   2,4-dichlorophenyl                                                                         oil                                        614  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   2-methylphenyl                                         615  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   4-methylphenyl                                         616  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   4-tert.-butylphenyl                                    617  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   2-naphthyl                                             618  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   2-fluorophenyl                                         619  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   4-bromophenyl                                          620  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   3-fluorophenyl                                         621  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sub.2                                                                   3,4-dichlorophenyl                                     622  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          phenyl                                                 623  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          2-methylphenyl                                         624  CH.sub.3                                                                              C(CH.sub.2 ).sub.5                                                                         4-methylphenyl                                         625  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          4-tert.-butylphenyl                                    626  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          2-naphthyl                                             627  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          2-fluorophenyl                                         628  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          3-fluorophenyl                                         629  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          4-fluorophenyl                                         630  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          4-bromophenyl                                          631  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          4-chlorophenyl                                         632  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          2-chlorophenyl                                         633  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          2,4-dichlorophenyl                                     634  CH.sub.3                                                                              C(CH.sub.2).sub.5                                                                          3,4-dichlorophenyl                                     635  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          phenyl                                                 636  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          2-methylphenyl                                         637  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          4-methylphenyl                                         638  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          4-tert.-butylphenyl                                    639  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          2-naphthyl                                             640  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          2-fluorophenyl                                         641  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          3-fluorophenyl                                         642  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          4-fluorophenyl                                         643  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          4-bromophenyl                                          644  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          4-chlorophenyl                                         645  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          2-chlorophenyl                                         646  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          2,4-dichlorophenyl                                     647  CH.sub.3                                                                              C(CH.sub.2).sub.4                                                                          3,4-dichlorophenyl                                     648  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   phenyl                                                 649  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   2-methylphenyl                                         650  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-methylphenyl                                         651  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-tert.-butylphenyl                                    652  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   2-naphthyl                                             653  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   2-fluorophenyl                                         654  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   3-fluorophenyl                                         655  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-fluorophenyl                                         656  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-bromophenyl                                          657  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-chlorophenyl                                         658  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   2,4-dichlorophenyl                                     659  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   3,4-dichlorophenyl                                     660  CH.sub.3                                                                              C(C.sub.2 H.sub.5).sup.n C.sub.4 H.sub.9                                                   4-biphenyl                                             ______________________________________                                    

Generally speaking, the novel compounds are extremely effective on a broad spectrum of phytopathogenic fungi, in particular those from the Ascomycetes and Basidiomycetes classes. Some of them have a systemic action and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling a large number of fungi in various crops or their seeds, especially wheat, rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee, sugar cane, fruit and ornamentals in horticulture and viticulture, and in vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling the following plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia species in cotton and lawns,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in vegetables and fruit.

The compounds are applied by spraying or dusting the plants with the active ingredients, or treating the seeds of the plants with the active ingredients. They may be applied before or after infection of the plants or seeds by the fungi. Either the fungi, or the plants, seed, materials or soil to be protected against fungus attack are treated with a fungicidally effective amount of the active ingredient.

The novel substances can be converted into conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient. The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are solvents such as aromatics (e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as ground natural minerals (e.g., kaolins, aluminas, talc and chalk) and ground synthetic minerals (e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates); and dispersants such as lignin, sulfite waste liquors and methylcellulose.

The fungicidal agents generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt % of active ingredient. The application rates are from 0.02 to 3 kg or more of active ingredient per hectare, depending on the type of effect desired. The novel compounds may also be used for protecting materials (wood), for example against Paecilomyces variotii.

When the active ingredients are used for treating seed, amounts of from 0.001 to 50, and preferably from 0.01 to 10, g are generally used per kg of seed.

The agents and the ready-to-use formulations prepared from them, such as solutions, emulsions, suspensions, powders, dusts, pastes and granules, are applied in conventional manner, for example by spraying, atomizing, dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. 90 parts by weight of compound no. 230 (Table 1) is mixed with 10 parts by weight of N-methyl-α-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 306 (Table 1) is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.

III. 20 parts by weight of compound no. 341 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and finely distributing it therein, an aqueous dispersion is obtained.

IV. 20 parts by weight of compound no. 382 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into water and uniformly distributing it therein, an aqueous dispersion is obtained.

V. 80 parts by weight of compound no. 175 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in water, a spray liquor is obtained.

VI. 3 parts by weight of compound no. 187 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

VII. 30 parts by weight of compound no. 191 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

VIII. 40 parts by weight of compound no. 253 is intimately mixed with 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water to give a stable aqueous dispersion. Dilution in water gives an aqueous dispersion.

IX. 20 parts by weight of compound no. 267 is intimately mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.

USE EXAMPLES

For comparison purposes, the compound 3-phenyl-2,2-dimethyl-1-(3-pyridyl)propan-1-ol (A) disclosed in EP 302,365 was used.

USE EXAMPLE 1 Action on Botrytis cinerea in pimientos

Pimiento seedlings of the "Neusiedler Ideal Elite" variety with 4 to 5 well developed leaves were sprayed to runoff with aqueous suspensions containing (dry basis) 80% of active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the plants were sprayed with a conidial suspension of the fungus Botrytis cinerea and kept in a high-humidity chamber at 22° to 24° C. After 5 days, the disease had spread on the untreated control plants to such an extent that the necroses covered the major portion of the leaves. The leaf attack was assessed.

The results show that active ingredients 230, 306, 341 and 382, applied as 0.05% spray liquors, have a better fungicidal action (90%) than prior art active ingredient A (55%).

USE EXAMPLE 2 Action on Pyrenophora teres

Barley seedlings of the "Igri" variety were sprayed to runoff at the two-leaf stage with aqueous suspensions consisting (dry basis) of 80% of active ingredient and 20% of emulsifier. After 24 hours the plants were inoculated with a spore suspension of the fungus Pyrenophora teres, and set up for 48 hours in a high-humidity climatic cabinet at 18° C. The plants were then cultivated for a further 5 days in the greenhouse at 20° to 22° C. and a relative humidity of 70° C. The extent of fungus spread was then assessed.

The results show that active ingredients 175, 187, 191, 253, 267, 306, 341 and 382, applied as 0.025% spray liquors, have a better fungicidal action (98%) than prior art active ingredient A (60%). 

We claim:
 1. A pyridine compound having the following formula: ##STR13## where R¹ is hydrogen or an acyl radical --COR² ; R² is C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -haloalkyl or substituted or unsubstituted aryl; A is one of the groups ##STR14## where R³ and R⁴ are identical or differ and each is C₁ -C₆ -alkyl, with the proviso that R³ and R⁴ are not simultaneously methyl; R⁵ is one of the groups (CH₂)_(n), CH₂ OCH₂, CH₂ S(O)_(m) CH₂, CH₂ CH₂ O or CH₂ CH₂ S(O)_(m), n denoting 1, 2, 3, 4 or 5, and m being 0, 1 or 2; Ar is phenyl, indanyl, 1-naphthyl, 2-naphthyl, 2-methyl-1-naphthyl or phenyl substituted by one to five substituents selected from the group consisting of C₁ -C₆ -alkyl, phenyl, halogen, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, or the N-oxide or plant-tolerated acid addition salt thereof.
 2. A fungicidal composition containing a carrier and a fungicidally effective amount of a pyridine compound of the formula ##STR15## where R¹ is hydrogen or an acyl radical --COR² ; R² is C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -haloalkyl or substituted or unsubstituted aryl; A is one of the groups ##STR16## where R³ and R⁴ are identical or differ and each is C₁ -C₆ -alkyl, with the proviso that R³ and R⁴ are not simultaneously methyl; R⁵ is one of the groups (CH₂)_(n), CH₂ OCH₂, CH₂ S(O)_(m) CH₂, CH₂ CH₂ O or CH₂ CH₂ S(O)_(m), n denoting 1, 2, 3, 4 or 5, and m being 0, 1 or 2; Ar is phenyl, indanyl, 1-naphthyl, 2-naphthyl, 2-methyl-1-naphthyl or phenyl substituted by one to five substituents selected from the group consisting of C₁ -C₆ -alkyl, phenyl, halogen, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, or the N-oxide or plant-tolerated acid addition salt thereof.
 3. A process for combating fungi, wherein the fungi, or the materials, plants, soils or seed threatened by fungus attack are treated with a fungicidally effective amount of a pyridine compound of the formula ##STR17## where R¹ is hydrogen or an acyl radical --COR² ; R² is C₁ -C₆ -alkyl, C₃ -C₆ -alkenyl, C₃ -C₆ -alkynyl, C₁ -C₆ -haloalkyl or substituted or unsubstituted aryl; A is one of the groups ##STR18## where R³ and R⁴ are identical or differ and each is C₁ -C₆ -alkyl, with the proviso that R³ and R⁴ are not simultaneously methyl; R⁵ is one of the groups (CH₂)_(n), CH₂ OCH₂, CH₂ S(O)_(m) CH₂, CH₂ CH₂ O or CH₂ CH₂ S(O)_(m), n denoting 1, 2, 3, 4 or 5, and m being 0, 1 or 2; Ar is phenyl, indanyl, 1-naphthyl, 2-naphthyl, 2-methyl-1-naphthyl or phenyl substituted by one to five substituents selected from the group consisting of C₁ -C₆ -alkyl, phenyl, halogen, C₁ -C₆ -haloalkyl, C₁ -C₆ -alkoxy, C₁ -C₆ -haloalkoxy, C₁ -C₆ -alkoxyiminocarbyl, phenoxy, halophenoxy and benzyloxy, or the N-oxide or plant-tolerated acid addition salt thereof. 